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In order to make a better informed response or suggestion, more information would be required of you......is the site for making $ or just for fun, how competive is the environment, would the capital time and investment work out if you sharpend a pencil to it.

I have a similar problem with a client of mine.While I feel on paper, their on-site SEO is below par. They are consistently ranking #1 and #2 for their keywords.

The one thing I have done was come up with a plan and structured it out in excel and word, just in case a large problem occurs.

The best solution would be to write out your proposed changes, and start small. If you start small and structure your plan in a timeline, you can re-structure the whole site over a long period of time without seeing any negative effects initially.

If all you are doing is creating a different architecture without making significant changes to the actual content (so giving each existing page a more SEO friendly category +/or file name) then you just need to make sure that every individual page is correctly redirected to its new URL using 301's. External links will remain in play and search engines will eventually recognize the redirects and update their indexes.

As long as you build the new structure in parallel so that you never take a page out of circulation you should be good.

If, on the other hand, you plan on altering content, removing pages completely, or doing something that will make existing pages unavailable for any period of time, you are likely to see some impact on rankings that might not be ideal.

If your concern stems from the fact that you are maybe not sure whether the new structure will actually help, then you will want to start slowly as Nicholas suggested.

My approach would be to do exactly as Nicholas described, but to start with pages that are ranking poorly.

So, basically, we are thinking of putting all content related to one keyword in a subdirectory. Currently all content is in one main subdirectory. For example, url.com/un-related-subdirectory/tons of content to url.com/keyword/content-related-to-this-keyword.

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